We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Holiday Rentals in Winchendon, MA

Payment Protection
Use a credit card to book with our Peace of Mind Protection.Learn more
Find a rental
Price per night
Min
Max
Bedrooms
Any
Amenities
Select
More filters
All 19 Rentals in the Winchendon Area
loading...
Sort by

The following rentals are within 30 kilometres of Winchendon, Massachusetts.

From
₹9,308
Per Night
View Details
1 / 18
Payment Protection
Barre
3 Bedrooms, 1 Bathroom, Sleeps 7
Bookings
Details Reviews (1) Make Enquiry
From
₹15,823
Per Night
View Details
1 / 32
Payment Protection
New Salem
4 Bedrooms, 3 Bathrooms, Sleeps 14
Bookings
Details Reviews (3) Make Enquiry
From
₹15,513
Per Night
View Details
1 / 36
Ashburnham
2 Bedrooms, 1 Bathroom, Sleeps 6
Details Reviews (14) Make Enquiry
From
₹12,410
Per Night
View Details
1 / 12
Payment Protection
Winchester, NH
4 Bedrooms, 1 Bathroom, Sleeps 9
Bookings
Details Reviews (2) Make Enquiry
Amenities & Details
  • Balcony
  • Dryer
  • Fireplace
  • Hot Tub
  • Internet Access
  • Mountain Views
  • Ping Pong Table
  • Private Fishing...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • Wheelchair access
  • Elder access
  • x
About this property
A Stunning Lakefront home on crystal clear,sandy bottomed, 110 acre Forest Lake at the junction of NH,VT,& MA will be your long awaited retreat in the whispering pines, shimmering lakes, and beautiful foliage of New Hampshire. Also check out our new home on Rockwood Pond in Fitzwilliam. NH! The... View all property information
Make Enquiry
5 of 5 stars Reviewed 14 October 2014
this large home is extremely well equipped. Each of our party had a separate bedroom and the communal spaces, and there are many of them, are extremely well equipped with...
See all reviews
From
₹12,410
Per Night
View Details
1 / 12
Payment Protection
Fitzwilliam, NH
3 Bedrooms, 2 Bathrooms, Sleeps 9
Bookings
Details Reviews (2) Make Enquiry
Amenities & Details
  • Balcony
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Hot Tub
  • Mountain Views
  • Ping Pong Table
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • Wheelchair access
  • Elder access
  • ?
About this property
3 Bedrooms (Queen, Queen and single) and an upstairs expansive family sleeping loft/entertainment center with a King,2 single beds and a hideabed. The great room has a full modern kitchen with all Brand New appliances, glasses, dishes, pots, spices, condiments and a dining table with room for 10.... View all property information
Make Enquiry
5 of 5 stars Reviewed 3 January 2013
With older family members in retirement housing in Keene, NH, we needed to find a way to continue our tradition of large family Christmas celebrations. When I found this Rockwood...
See all reviews
From
₹6,205
Per Night
View Details
1 / 21
Payment Protection
Winchester, NH
2 Bedrooms, 1 Bathroom, Sleeps 6
Details Reviews (3) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
  • Waterfront
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
2 Bedrooms, 1 bath, sleeps 6. Private beach, dock, raft, rowboat, canoe, 4 Kayaks, or launch your boat. Cable TV, high speed internet, WIFI, 42' flat screen internet TV. Sleeps 6 - two bedrooms - One with Queen Bed, one with two single beds, and a full size pullout couch in the family/living... View all property information
Make Enquiry
5 of 5 stars Reviewed 30 September 2014
Great off the beaten track place to stay yet only 20 minutes from Keene. Bill and Sandie very gracious hosts both before and during your stay. Accommodations very modern. We will...
5 of 5 stars Reviewed 13 July 2014
My fiancé and another couple stayed here for a few days in May. It was absolutely beautiful and exactly what we were looking for! My fiancé and I are avid "outdoors people" and...
See all reviews
From
₹74,460
Per Week
View Details
1 / 24
Payment Protection
Rindge, NH
2 Bedrooms, 1 Bathroom, Sleeps 7
Bookings
Details Reviews (1) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Grill
  • Satellite TV
  • Waterfront
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Here is the perfect location for your family vacation or a couple's getaway. Pearly Pond offers all of your favorite outdoor activities. Choose from swimming, canoeing (kayaking), hiking, mountain biking or fishing. If you're more into relaxing, just stretch out on the deck with your favorite... View all property information
Make Enquiry
4 of 5 stars Reviewed 25 June 2014
My daughter was graduating from Franklin Pierce University and we were coming to her graduation. This cottage is only a few miles from the Rindge campus - and to top it off, its...
See all reviews
From
₹12,410
Per Night
View Details
1 / 28
Payment Protection
Jaffrey, NH
6 Bedrooms, 8 Bathrooms, Sleeps 12
Bookings
Details Make Enquiry
Amenities & Details
  • Balcony
  • Dishwasher
  • Dryer
  • Internet Access
  • Mountain Views
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
1) Beautiful historic property, originally an early 1800's tavern with a rich history as a working farm, seasonal vacation home, inn and year round residence. Property sits at the base of Mt. Monadnock with beautiful mountain and pastoral views. Our street address is 580 Mountain Rd., Jaffrey, NH... View all property information
Make Enquiry
From
₹7,446
Per Night
View Details
1 / 1
Payment Protection
Richmond, NH
2 Bedrooms, 1 Bathroom, Sleeps 4
Details Make Enquiry
Amenities & Details
  • Air Conditioning
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Enjoy a quiet entire apartment with your friend and family in historic town Richmond,Va This is a apartment on first floor in byrd park area with all renovation, it is between byrd park and Cary town (good neighborhood) first floor apartment has a 1 year lease tenant live there. it is pretty... View all property information
Make Enquiry
From
₹185,840
Per Month
View Details
1 / 10
Payment Protection
Richmond, NH
2 Bedrooms, 3 Bathrooms, Sleeps 3
Details Make Enquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Stunningly beautiful two bedroom, t.5 bath condominium in the Oregon Hill section of Richmond, along the James River within easy walking access to the Canal Walk, numerous restaurants and with the heart of downtown Richmond less than five minutes away; walk if you feel like it. Rents fully... View all property information
Make Enquiry
Get the List
From
₹37,230
Per Night
View Details
1 / 11
Harrisville, NH
6 Bedrooms, 4 Bathrooms, Sleeps 16
Details Make Enquiry
Amenities & Details
  • Dishwasher
  • Dryer
  • Fireplace
  • Hot Tub
  • Internet Access
  • Mountain Views
  • Safe
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
750 Acre (300 Hectare) Estate! 5 Bedrooms + Detached Unit - 4.5 Baths - (Sleeps 14-15) This enormous estate is one of a kind! The rental includes the a Main House, the Sunset/Guest Cabin, secret Treehouse, and private land larger than many towns! Although the estate is often enjoyed for... View all property information
Make Enquiry
From
₹9,308
Per Night
View Details
1 / 9
Payment Protection
Jaffrey, NH
3 Bedrooms, 1 Bathroom, Sleeps 6
Booking
Details Make Enquiry
Amenities & Details
  • Dishwasher
  • Fireplace
  • Grill
  • Internet Access
  • Wi-Fi
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Nestled at the base of the mountain, sits our log cabin. A quiet, country area with neighbors within walking distance but not within view. Perennial flowers and trees surround the property with a brook for a backdrop, as well as an expanse of lawn for yard games and campfire. Inside you'll... View all property information
Make Enquiry
From
₹13,589
Per Night
View Details
1 / 20
Payment Protection
Fitzwilliam, NH
3 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Enquiry
Amenities & Details
  • Dryer
  • Internet Access
  • Private Fishing...
  • Satellite TV
  • Washer
  • Waterfront
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
Come to Twin Tree Lodge for an escape from stress and the city! Our location is perfect for fall foliage and visiting farms for maple syrup, apples, and cider. We are on Scott Pond and in the shadow of Gap Mountain and Mount Monadnock, as well as the Cheshire Rail Trail, lots of covered bridges... View all property information
Make Enquiry
From
₹6,205
Per Night
View Details
1 / 4
Payment Protection
Princeton
2 Bedrooms, 2 Bathrooms, Sleeps 5
Details Make Enquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
So awesome, its so awesome. So awesome, its so awesome. So awesome, its so awesome. So awesome, its so awesome. So awesome, its so awesome. So awesome, its so awesome. So awesome, its so awesome. So awesome, its so awesome. So awesome, its so awesome. So awesome, its so awesome. So awesome, its so... View all property information
Make Enquiry
From
₹47,779
Per Week
View Details
1 / 21
Payment Protection
Peterborough, NH
2 Bedrooms, 1 Bathroom, Sleeps 4
Booking
Details Make Enquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
An easy one mile walk from downtown Peterborough (sidewalks all the way) with all its fantastic shopping, dining, parks, and quintessential New England charm. This recently renovated two bedroom riverside cottage sleeps four people. With its updated kitchen, spacious living room, screened-in porch,... View all property information
Make Enquiry
From
₹6,639
Per Night
View Details
1 / 18
Rindge, NH
3 Bedrooms, 1 Bathroom, Sleeps 7
Details Make Enquiry
Amenities & Details
  • Dryer
  • Grill
  • Satellite TV
  • Washer
  • Waterfront
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
On the Lake, 80 Feet Sandy Beach Frontage, facing west with beautiful sunset view Docks and Nice Swimming Area all part of this nice private property NEW DOCKS MAY 2014 Patio spaces at the Beach Picnic Tables/Barbeque Area (all part of the property) Sunny Deck (NEW DECK MAY May 2011!!)... View all property information
Make Enquiry
From
₹18,305
Per Night
View Details
1 / 26
Payment Protection
New Ipswich, NH
3 Bedrooms, 3 Bathrooms, Sleeps 12
Booking
Details Make Enquiry
Amenities & Details
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Hot Tub
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Home built in 2000 with complete makeover in 2013 features hardwood and tile floors throughout, granite kitchen countertops, fridge, dishwasher, gas stove, microwave, toaster, coffee maker, washer, dryer, whirlpool tub, central vac, gas grill, and gas fireplace. All new furniture in 2014 throughout... View all property information
Make Enquiry
From
₹31,025
Per Night
View Details
1 / 13
Harrisville, NH
5 Bedrooms, 5 Bathrooms, Sleeps 15
Details Make Enquiry
Amenities & Details
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Hot Tub
  • Internet Access
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
This enormous estate is one of a kind! The rental includes the a Main House, the Sunset/Guest Cabin, secret Treehouse, and private land larger than many towns! Although the estate is often enjoyed for inexpensive weddings, family gatherings, reunions, and corporate retreats, it is also enjoyed... View all property information
Make Enquiry
Inquire for rates
1 / 20
Rindge, NH
3 Bedrooms, 1 Bathroom, Sleeps 8
Details Make Enquiry
Amenities & Details
  • Air Conditioning
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Called 'A little slice of heaven' by one renter, this scenic property captures the beauty of rural New England. The cabin is a modernized 1903 cottage with 1100 square feet of comfortable living space that includes three bedrooms, living room, dining room, kitchen and one full bathroom. Fully... View all property information
Make Enquiry
Go to map view
Book Online(14)
Use filters to find the best results!

Suitability

  • Wheelchair access (1)
  • Elder access (6)
  • Suitable for children (6)
  • Pet friendly (4)
  • Smoking allowed (0)

Amenities

  • Other outdoor space (14)
  • Parking (14)
  • Internet (12)
  • Washer/Dryer (12)
  • Grill (11)
  • View all amenities
List your property for free!
List your accommodation
for free on our website.
Reach millions worldwide.
Add a Listing


In partnership with
Get the List
Nearby cities